P,P-Diphenylphosphinic azide → HCID 86721002, compound

HRID 524944Notes

Reaction equation

HRID 524944 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]2[CH:15]=[N:14][CH:13]=[C:12](C(O)=O)[C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:35]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN1C(=O)CCC1>[NH2:35][C:12]1[CH:13]=[N:14][CH:15]=[C:16]2[C:11]=1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17]2

Participants

4

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 847148112,7-Naphthyridine-2,5(1H)-dicarboxylic acid, 3,4-dihydro-, 2-(1,1-dimethylethyl) ester

Product 1

HCID 86721002HCID 86721002, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 7-tert-butoxycarbonyl-6,8-dihydro-5H-2,7-naphthyridine-4-carboxylic acid (440 mg, 1.581 mmol) in NMP (6 mL) was added TEA (207.9 mg, 286.4 μL, 2.055 mmol) followed by diphenylphosphoryl azide (478.6 mg, 374.8 μL, 1.739 mmol) at rt under nitrogen. The reaction was heated to 90° C. for 2 hours. At RT, the reaction mixture was partitioned between an aqueous saturated solution of NaHCO3 and EtOAc. Combined organic extract was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica, eluting with 1-15% MeOH:DCM to yield tert-butyl 5-amino-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate. (397 mg, 100.7%). MS (2ES+) 501.2.

Workup

  1. customAt RT, the reaction mixture was partitioned between an aqueous saturated solution of NaHCO3 and EtOAc
  2. extractionCombined organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica
  7. washeluting with 1-15% MeOH

Sources & evidence

ORD record
ord-d0895b005fc84497a3cf56ce1016a9ca
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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